HCID 21290645, compound → HCID 21290634, compound

HRID 280693Notes

Reaction equation

HRID 280693 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[C:4](Cl)[N:3]=1.[H][H]>C(O)(=O)C.O.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:11][CH2:10]2)=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 21290645HCID 21290645, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21290634HCID 21290634, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

21.5 g of 2,4-diamino-6-chloro-5-[1-(4-methoxyphenyl)-4-piperidinyl]pyrimidine were dissolved in 350 ml of a mixture of acetic acid and water (1:1) and hydrogenated in the presence of 7 g of 10% palladium/carbon catalyst until the hydrogen uptake ceased or the reaction was complete in accordance with thin-layer chromatography. The catalyst was filtered off over a filter aid and the filtrate was evaporated to dryness. The residue was suspended in water and the pH was adjusted to 9 by addition of aqueous ammonium hydroxide. Filtration yielded a crude product which was chromatographed on silica gel with chloroform/methanol (19:1). There were obtained 8.7 g of 2,4-diamino-5-[1-(4-methoxyphenyl)-4-piperidinyl]pyrimidine of melting point 224°-225° C.

Workup

  1. filtrationThe catalyst was filtered off over a filter aid
  2. customthe filtrate was evaporated to dryness
  3. additionthe pH was adjusted to 9 by addition of aqueous ammonium hydroxide
  4. filtrationFiltration
  5. customyielded a crude product which
  6. customwas chromatographed on silica gel with chloroform/methanol (19:1)

Sources & evidence

ORD record
ord-43f00ba3e23740b9868341f5183a8bd3
Source dataset
uspto-grants-1986_05
Patent number
US04590270

Reaction notes

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